TW202302551A - 用於製備４－側氧四氫呋喃－２－羧酸烷基酯之方法 - Google Patents
用於製備４－側氧四氫呋喃－２－羧酸烷基酯之方法 Download PDFInfo
- Publication number
- TW202302551A TW202302551A TW111107295A TW111107295A TW202302551A TW 202302551 A TW202302551 A TW 202302551A TW 111107295 A TW111107295 A TW 111107295A TW 111107295 A TW111107295 A TW 111107295A TW 202302551 A TW202302551 A TW 202302551A
- Authority
- TW
- Taiwan
- Prior art keywords
- general formula
- compound
- cyclization
- iii
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- -1 alkyl 4-oxotetrahydrofuran-2-carboxylate Chemical compound 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 238000005933 dealkoxycarbonylation reaction Methods 0.000 claims description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 229910052700 potassium Chemical group 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 239000000047 product Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 238000007083 alkoxycarbonylation reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- UWONJGBQYPCSEH-UHFFFAOYSA-N 4-oxooxolane-2-carboxylic acid Chemical compound O=C1CC(OC1)C(=O)O UWONJGBQYPCSEH-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21160525.8 | 2021-03-03 | ||
| EP21160525.8A EP4053112A1 (de) | 2021-03-03 | 2021-03-03 | Verfahren zur herstellung von substituiertem 4-oxo-tetrahydrofuran |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW202302551A true TW202302551A (zh) | 2023-01-16 |
Family
ID=74858208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW111107295A TW202302551A (zh) | 2021-03-03 | 2022-03-01 | 用於製備４－側氧四氫呋喃－２－羧酸烷基酯之方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20240166616A1 (de) |
| EP (2) | EP4053112A1 (de) |
| JP (1) | JP2024509535A (de) |
| KR (1) | KR20230154214A (de) |
| CN (1) | CN116888104A (de) |
| IL (1) | IL305616A (de) |
| MX (1) | MX2023010286A (de) |
| TW (1) | TW202302551A (de) |
| WO (1) | WO2022184611A1 (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6999424B2 (ja) | 2015-06-18 | 2022-01-18 | エイティナイン バイオ リミテッド | １，４－置換ピペリジン誘導体 |
| LT3638665T (lt) | 2017-06-13 | 2021-09-27 | Bayer Aktiengesellschaft | Tetrahidro- ir dihidrofurankarboksirūgščių ir esterių herbicidiniai 3-fenilizoksazolin-5-karboksamidai |
-
2021
- 2021-03-03 EP EP21160525.8A patent/EP4053112A1/de not_active Ceased
-
2022
- 2022-02-28 US US18/548,530 patent/US20240166616A1/en active Pending
- 2022-02-28 EP EP22708153.6A patent/EP4301740A1/de active Pending
- 2022-02-28 JP JP2023553361A patent/JP2024509535A/ja active Pending
- 2022-02-28 CN CN202280017900.XA patent/CN116888104A/zh active Pending
- 2022-02-28 WO PCT/EP2022/054924 patent/WO2022184611A1/de active Application Filing
- 2022-02-28 KR KR1020237033181A patent/KR20230154214A/ko unknown
- 2022-02-28 IL IL305616A patent/IL305616A/en unknown
- 2022-02-28 MX MX2023010286A patent/MX2023010286A/es unknown
- 2022-03-01 TW TW111107295A patent/TW202302551A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP4053112A1 (de) | 2022-09-07 |
| CN116888104A (zh) | 2023-10-13 |
| US20240166616A1 (en) | 2024-05-23 |
| WO2022184611A1 (de) | 2022-09-09 |
| MX2023010286A (es) | 2023-09-11 |
| KR20230154214A (ko) | 2023-11-07 |
| JP2024509535A (ja) | 2024-03-04 |
| EP4301740A1 (de) | 2024-01-10 |
| IL305616A (en) | 2023-11-01 |
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